Sodium Nitrate → Methyl 5-nitroisoquinoline-3-carboxylate

HRID 585933

Reaction equation

HRID 585933 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13][CH3:14])=[O:12])[N:2]=1.[N+:15]([O-])([O-:17])=[O:16].[Na+]>OS(O)(=O)=O>[N+:15]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[C:3]([C:11]([O:13][CH3:14])=[O:12])[N:2]=[CH:1]2)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 725374Methyl 3-isoquinolinecarboxylate

Product 1

HCID 22032663Methyl 5-nitroisoquinoline-3-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Methyl isoquinoline-3-carboxylate (9.58 g, 51.2 mmol) in concentrated H2SO4 (100 mL) at 0° C. was treated with sodium nitrate (4.79 g, 56.4 mmol) in small portions such that the temperature was maintained below 5° C. Ten minutes after addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The mixture was poured over ice and adjusted to pH between 7 and 8 and filtered to afford the title compound as a bright yellow solid (11.44 g, 96%). MS (ESI+) m/z 233 (M+H)+; 1H NMR (DMSO, 300 MHz) δ 3.97 (s, 3H), 8.06 (t, J 8.2, 1H), 8.72 (dt, J 1.0, 8.2, 1H), 8.78 (dd, J 1.0, 7.8, 1H), 9.11 (s, 1H), 9.65 (s, 1H).

Workup

  1. temperaturewas maintained below 5° C
  2. additionTen minutes after addition
  3. additionThe mixture was poured over ice
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e60dc71fb82a4380a91080f19587b677
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Linked notes

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